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Experiences Along the Great Chesapeake Bay Loop

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Lighthouse at Chesapeake Bay Maritime Museum
Chesapeake Bay Maritime Museum
Photo By: Chesapeake Bay Maritime Museum
eating crabs by the water
Steamed crabs
Chesapeake Bay Bridge Photo By: OTD

1 25 Can’t-Miss Things to Do Along the Chesapeake Bay

Play, sight-see, eat, socialize, collect and explore along Maryland’s famous estuary. Use these 25 ideas for things to see and do along the Chesapeake to get you going.

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Calvert Marine Museum Megaladon Shark Photo By: Calvert Marine Museum

2 Things to See and Do in Southern Maryland

In Southern Maryland, history and culture mingle on the shores of the Chesapeake Bay. 

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Cruise up in your boat to Ego Alley, or come on foot and marvel at the beautiful boats.

3 Things to See and Do in Central Maryland

From Annapolis—Maryland’s capital city and the Sailing Capital of the World—to the bustling metropolis of Baltimore, to the Piedmont forests and the shores of the Chesapeake Bay, the Central Region offers thriving cultural destinations, history, music and more.

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Family on the beach with ponies

4 Things to See and Do on the Eastern Shore

Maryland’s Eastern Shore is home to spectacular sunsets, world-class seafood and produce, nature, history and so much more.

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Guitar building Photo By: Paul Reed Smith Guitars

5 Nifty off 50

U.S. Route 50 is the major east-west route of the U.S. Highway system and it starts and  cuts right through Maryland. Be sure to see the unique places and people along this iconic road.

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Waterfowl painting

6 Art of the Chesapeake

Discover the best galleries and arts events and learn about the unique art of Maryland’s Chesapeake Bay.

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Be inspired at this important War of 1812 site and birthplace of The National Anthem. Photo By: Ken Stanek Photography

7 National and State Parks

Get in touch with the lives of great Americans like Harriet Tubman, Clara Barton and Thomas Stone. See historic places like Fort McHenry and the Chesapeake and Ohio Canal where the very course of history was changed. Lose yourself in one of a kind landscapes at public parks like Assateague, Sandy Point and Blackwater.

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Waterfront Photo By: CBMM

8 Maryland’s Maritime Museums

Maryland's maritime museums offer so much to explore.  Touch and experience the Chesapeake Bay's marine creatures up-close and discover how they live.  Explore a boat-building workshop and get an insider's look at the life of a waterman.  She how people depend upon a healthy bay.

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9 Tour Maryland’s Lighthouses

Tour these beautiful historic beacons and enjoy the surrounding nature and vistas of the Chesapeake Bay.

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Enjoy breathtaking sunsets at Solomons Island. Photo by Southern Maryland Photography Photo By: Southern Maryland Photography

10 Touring the Islands of Maryland

Maryland is home to hundreds of islands just waiting to be explored. Some are uninhabited or strictly nature preserves, while others are bustling with shops, restaurants and museums.

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Crew on a sailboat Photo By: Jill Jasuta

11 Boating and Water Sports

Maryland's waterways are a defining feature of the Old Line State, and no visit is complete without leaving the land behind, even for just a little while. 

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travel the crab & oyster trail Photo By: motoxdms-Instagram

12 Maryland Crab & Oyster Trail

Savor the fruits of the Chesapeake Bay on the Maryland Crab & Oyster Trail.

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Purple Wine Photo By: Romano Vineyard

13 Wine Trails Along the Great Chesapeake Bay Loop

Maryland’s distinct microclimates provide diversity and flavor to our wines. Three of the Maryland’s eight wine trails are part of the Great Chesapeake Bay Loop.

Chesapeake Wine Trail, this trail is the perfect excuse to explore the treasures of the Eastern Shore

Legacy Wine Trail,  Southern Maryland's agricultural heritage meets the new legacy of fine wine.

Patuxent Wine Trail, Southern Maryland capitalizes on its Old-World growing traditions to bring an exciting new vision to classic wine profiles.

eating crabs by the water

14 Waterside Events and Festivals

Whether you want to make a splash or just watch, waterside events abound in Maryland.

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Chesapeake Bay Sunset Photo By: motoxdms-instagram-

15 More About the Great Chesapeake Bay Loop

To help you plan your Chesapeake Bay adventure, here’s some suggestions to get the most memories per mile:

Travel Around the Chesapeake Bay Loop

Quintessential Chesapeake Bay Towns

Stay Along the Great Chesapeake Bay Loop

Trip Suggestions for the Great Chesapeake Bay Loop

About the Great Chesapeake Bay Loop

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Chesapeake Bay Bridge
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Enjoy breathtaking sunsets at Solomons Island. Photo by Southern Maryland Photography
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Want to get away to the islands? Maryland is home to hundreds of islands just waiting to be explored! Some are uninhabited or strictly nature preserves, while others are...

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Search our list of Maryland breweries, wineries and distilleries here.

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Quintessential Chesapeake Bay Towns

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People on a boat crossing the bay to St. Michaels
Trip Suggestions for the Great Chesapeake Bay Loop

With the Great Chesapeake Bay Loop the miles of adventure are unlimited. Explore for a day, escape for a long weekend, or spend a vacation week, or more, enjoying all there is...

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Chesapeake Bay Bridge
Great Chesapeake Bay Loop

Plan your Chesapeake Bay adventure

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